Generation of Triplet Excited States via Photoinduced Electron Transfer in meso-anthra-BODIPY: Fluorogenic Response toward Singlet Oxygen in Solution and in Vitro
Generation of Triplet Excited States via Photoinduced Electron Transfer in meso-anthra-BODIPY: Fluorogenic Response toward Singlet Oxygen in Solution and in Vitro
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DOI：
10.1021/jacs.7b00551
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发表时间：
2017-05-10
影响因子：
15
通讯作者：
Senge, Mathias O.
中科院分区：
文献类型：
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作者：
Filatov, Mikhail A.;Karuthedath, Safakath;Senge, Mathias O.
无重原子bodipy -蒽二偶体（BADs）通过光诱导电子转移（PeT）产生局域激发三重态，然后由电荷分离态（CSS）重组。随后三态被分子氧猝灭产生单线态氧（O-1(2)），它与蒽部分反应产生高荧光物质。BODIPY亚基上烷基取代基的空间需求决定了O-1(2)加成的位置。从蒽内过氧化物的重排反应中分离并鉴定了新的双环氧化合物、四环氧化合物和双环缩醛化合物。BADs在活细胞中生成O-1(2)，使二偶体分布可视化，有望实现新的成像应用。
Heavy atom-free BODIPY-anthracene dyads (BADs) generate locally excited triplet states by way of photoinduced electron transfer (PeT), followed by recombination of the resulting charge-separated states (CSS). Subsequent quenching of the triplet states by molecular oxygen produces singlet oxygen (O-1(2)), which reacts with the anthracene moiety yielding highly fluorescent species. The steric demand of the alkyl substituents in the BODIPY subunit defines the site of O-1(2) addition. Novel bis- and tetraepoxides and bicyclic acetal products, arising from rearrangements of anthracene endoperoxides were isolated and characterized. O-1(2) generation by BADs in living cells enables visualization of the dyads distribution, promising new imaging applications.